Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- Millside Cottage
- Dale Cottage Retreat
- Alice Cottage
- Snake And Diamond Cottage
- Stonecroft
- The Stables Northwood Farm
- The Old Stable In The Peaks
- Brosterfield Suite
- Lower Ivy
- Fern Cottage Buxton
- Thorpe Cottage
- Green Pastures Cottage
- Church Quarters
- Top Tack
- Church Gates Cottage
- Poppies Court
- The Old Weighbridge
- Stowe Cottage
- Harebell Hill
- Damson Jam
- Mulberry Cottage Peak
- Common Bank Cottage
- Railway Cottage
- Pipistrelle Barn
- Waldley Cottage
- Little Hillside
- The Coach House At Blackbrook House
- The Old Barn At Carsington
- Swallows Nest Cottage
- Thrift Cottage
Winster Holiday Cottages
Our curated collection of Winster cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Winster holiday home today.
Visitor Rating
4.5
- Grade II-listed cottage in Winster
- Wood burner and roof terrace
- King-size bedroom with window seat
- Village shop just yards away
- One dog welcome to stay
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- Stone cottage in conservation village
- Wood burner and Smart TV lounge
- Sleeps 3 with flexible bedroom
- Enclosed garden welcomes two dogs
- Walking distance to Limestone Way
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Visitor Rating
4
- Grade II listed 300-year-old cottage
- Woodburner in gritstone fireplace
- Walking distance to village amenities
- Garden with study room access
- Peak District location near Matlock
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- Private enclosed woodland garden
- Wood burner lounge
- Peak District walking on doorstep
- One dog welcome
- 2 miles from Glossop
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Visitor Rating
4
- Single-level cottage for two
- Mature gardens with rolling views
- Peak District walking routes nearby
- En-suite bedroom with garden outlook
- Enclosed courtyard with outdoor seating
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Visitor Rating
4.6
- Panoramic Peak District countryside views
- Converted stone barn sleeping two
- Welcome up to three dogs
- Enclosed patio with outdoor dining
- Walking distance to local pub
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- Log burner in cosy living room
- Up to three dogs welcome
- Walk to Torrs Gorge & Sett Valley Trail
- Enclosed private garden
- Secure lockable bike storage
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Visitor Rating
4.8
- Kinder Scout walks from door
- Wood burner and two sitting rooms
- King-size bedroom with en-suite shower
- Enclosed garden with Peak views
- Village location with pubs nearby
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Visitor Rating
4
- Direct access to Kinder Scout trails
- Stone cottage sleeping three guests
- Open fire in lounge area
- Elevated garden with countryside views
- Two dogs welcome throughout cottage
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Visitor Rating
3
- Adjacent to Kinder Scout path
- Spectacular Dark Peak views everywhere
- Wood burner in beamed lounge
- Sleeps four in two bedrooms
- Dog friendly walking paradise
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- Four-storey townhouse sleeping six to eight
- Two dogs welcome with Peak walks
- Modern kitchen with dishwasher and utility
- Two separate living rooms across floors
- Near Bugsworth Basin and Lyme Park
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Visitor Rating
4
- Two pubs one minute away
- Private garden and decking
- Walks to Kinder Scout from door
- Well-equipped kitchen and utility room
- Peak District on the doorstep
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating and wood burner
- Walks directly from the door
- Welcomes up to three dogs
- Peaceful end-of-lane converted coach house
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating throughout
- Wood burner and leather seating
- Welcomes up to 3 dogs
- Peak District countryside location
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Visitor Rating
4.6
- Part of Georgian mansion grounds
- Wood burner and flagstone floors
- Welcomes three dogs
- Extensive woodland walking routes
- Double with Juliet balcony views
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Visitor Rating
4
- 18th-century barn with countryside views
- Two en-suite bedrooms sleeping four
- Kitchen garden with organic produce
- Wood pellet heating and underfloor warmth
- Walking and cycling from doorstep
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Visitor Rating
4
- Upside-down cottage with valley views
- Log burning stove and cosy sofas
- Walks from door across Peak moorland
- Two bathrooms including walk-in shower
- Sleeps four with two ground bedrooms
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Visitor Rating
4
- Woodland setting with babbling stream
- Sleeps 4 in 2 bedrooms
- Wood burner and vaulted ceilings
- Kinder Scout on the doorstep
- Welcomes 2 dogs with parking
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Visitor Rating
4
- Ground-floor barn conversion for two
- Welcomes two dogs to Peak District
- Floor-to-ceiling windows with tree views
- King-size bedroom with shower room
- Shared gardens with BBQ and stream
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Visitor Rating
4
- Woodburner with logs provided
- Adjacent village pub dining
- Hillside walks from doorstep
- Two dogs welcome
- Countryside views from bedroom
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Visitor Rating
4
- Sleeps 2 on working farm
- Wood burner with logs included
- Two bathrooms off bedroom
- Mountain bike secure storage
- Stunning Peak District countryside views
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- King-size four-poster bed
- Private garden with country views
- Stone cottage with gas stove
- Direct Peak District walking access
- One dog welcome
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- Traditional Peak District barn conversion
- Stream-side garden with country views
- 1.2 miles from Castleton village
- Wood burner and freestanding bath
- One dog welcome
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- Secluded Peak District farmland location
- Mam Tor views from the terrace
- Wood burner for all seasons
- 0.5 miles from Castleton village
- On the Great Ridge walking route
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- Original wood burner and beams
- Panoramic Peak District views
- Private patio with BBQ and chiminea
- Steps from Castleton village pubs
- Walk to Mam Tor and show caves
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Visitor Rating
4.4
- Former bakery with original features
- Sleeps 4 in two bedrooms
- Three-tiered garden with summer house
- Mam Tor views from top tier
- Central Castleton village location
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Visitor Rating
4
- Walks directly from the cottage door
- Wood burner in stone fireplace
- Hope railway station in village
- Secluded courtyard garden with seating
- Recently renovated throughout
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Visitor Rating
4
- Sleeps 6 in Hope Valley
- Two dogs welcome with garden
- Three bedrooms in characterful cottage
- Walking distance to Hope village
- Pennine Way on the doorstep
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Visitor Rating
4
- Converted barn under Winn Hill
- Sleeps four with two bedrooms
- Two dogs welcome with gardens
- Hope Valley views from living space
- Half mile to Hope train station
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- Converted barn with original features
- Sleeps 2 in mezzanine bedroom
- Free-standing bath and walk-in shower
- Peak District National Park location
- Walking trails from your door
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Explore more of Derbyshire
Popular towns and villages in and around Winster
Alfreton Ashbourne Bakewell Bamford Baslow Beeley Belper Bonsall Buxton Castleton Chatsworth Chellaston Chelmorton Chesterfield Chinley Clay Cross Cromford Darley Dale Denby Dronfield Edale Eyam Glossop Hadfield Hartington Hathersage Hayfield Heath Holmesfield Hulland Ward Kirk Ireton Kirk Langley Matlock Matlock Bath Over Haddon Somercotes South Wingfield Tansley Tideswell Tissington Whaley Bridge Wirksworth Youlgreave